CN101260416A - Technique for preparing 1,3-diglyceride by enzyme method - Google Patents
Technique for preparing 1,3-diglyceride by enzyme method Download PDFInfo
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- CN101260416A CN101260416A CNA2008101050801A CN200810105080A CN101260416A CN 101260416 A CN101260416 A CN 101260416A CN A2008101050801 A CNA2008101050801 A CN A2008101050801A CN 200810105080 A CN200810105080 A CN 200810105080A CN 101260416 A CN101260416 A CN 101260416A
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- lipase
- lipid acid
- triglyceride
- fatty acid
- ester
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- 108090000790 Enzymes Proteins 0.000 title claims description 13
- 102000004190 Enzymes Human genes 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 68
- 235000011187 glycerol Nutrition 0.000 claims abstract description 34
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims abstract description 24
- 108090001060 Lipase Proteins 0.000 claims abstract description 19
- 239000004367 Lipase Substances 0.000 claims abstract description 19
- 102000004882 Lipase Human genes 0.000 claims abstract description 19
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 19
- 229930195729 fatty acid Natural products 0.000 claims abstract description 19
- 239000000194 fatty acid Substances 0.000 claims abstract description 19
- 235000019421 lipase Nutrition 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 14
- 235000021588 free fatty acids Nutrition 0.000 claims abstract description 9
- 239000002808 molecular sieve Substances 0.000 claims abstract description 9
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 9
- -1 fatty acid ester Chemical class 0.000 claims abstract description 6
- 238000006911 enzymatic reaction Methods 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 29
- 150000002632 lipids Chemical class 0.000 claims description 29
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 21
- 230000009466 transformation Effects 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 6
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 5
- 241001661345 Moesziomyces antarcticus Species 0.000 claims description 3
- 241000235403 Rhizomucor miehei Species 0.000 claims description 3
- 241000223258 Thermomyces lanuginosus Species 0.000 claims description 3
- 125000004494 ethyl ester group Chemical group 0.000 claims description 3
- 240000005384 Rhizopus oryzae Species 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 238000012856 packing Methods 0.000 claims description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 2
- 150000003626 triacylglycerols Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- 239000012429 reaction media Substances 0.000 abstract description 4
- 230000002255 enzymatic effect Effects 0.000 abstract description 3
- 230000003044 adaptive effect Effects 0.000 abstract 1
- 150000001982 diacylglycerols Chemical class 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 108010048733 Lipozyme Proteins 0.000 description 8
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 6
- 239000005642 Oleic acid Substances 0.000 description 6
- 235000021355 Stearic acid Nutrition 0.000 description 6
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 6
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 6
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 6
- 239000008117 stearic acid Substances 0.000 description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 5
- 108010084311 Novozyme 435 Proteins 0.000 description 4
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention discloses a technology for preparing 1, 3-diacylglycerol by an enzymatic method, and relates to the diacylglycerol technical field. The steps of the technology are as follows: putting glycerin and fatty donor with a molar ratio of 1:0.5 to 1:3, tert-butyl alcohol of 20 to 200 percent of the weight of the fatty donor, lipase of 2 to 20 percent of the weight of the fatty acid, and 3 angstrom molecular sieve of 10 to 100 percent of the weight of the free fatty acid together into any biochemical reactor adaptive for enzymatic reaction to be uniformly mixed; the temperature is controlled between 30 and 65 DEG C and the reaction time is 1 to 10 hours. The percent conversion from glycerin to diglyceride can reach 70 to 90 percent. The content of 1, 3-diacylglycerol in the diglyceride can reach more than 60 percent. The fatty acid donor comprises fatty acid, fatty acid ester or mixture thereof. The technology has the advantages that the tert-butyl alcohol is adopted as reaction medium, and the glycerin can be effectively dissolved in the tert-butyl alcohol system; beside the lipase, the reaction is a homogeneous system, and the enzymatic percent conversion is improved apparently.
Description
Technical field
The present invention relates to the triglyceride technical field, particularly a kind of enzyme process preparation 1,3-triglyceride technology, with the trimethyl carbinol as reaction medium, produce triglyceride by the esterification between lipase-catalyzed glycerine and the different lipid acid donors, especially 1, the 3-triglyceride.
Background technology
Triglyceride can be used as emulsifying agent, fatty plasticity improving agent or is used as the matrix of food, medicine, makeup etc.On structure, triglyceride is a kind of the fat mols with two fatty acid chains, and two kinds of isomerss are arranged, promptly 1, and 2-triglyceride and 1,3-triglyceride.Discovering in recent years, 1, the 3-triglyceride is in the intravital absorption metabolic way of people and triglyceride level and 1, the difference of 2-triglyceride.Eat and contain 1, the grease of 3-triglyceride has the effect that prevents weight increase.
The following method of the synthetic employing of the enzyme process of common triglyceride: the 1) glycerolysis reaction of triglyceride level and glycerine; 2) esterification of glycerine and lipid acid; 3) the incomplete hydrolysis of triglyceride level.First method exists that reaction substrate viscosity is big, speed of response is slow, the by product free fatty acids is many and problem such as separation difficulty, makes the production cost of triglyceride raise; The third method exists that reaction is wayward, by product many and shortcoming such as separation difficulty.The second method speed of response is very fast, and is simple and easy to do.But glycerine is polar molecule, and the consistency under the enzyme reaction condition between glycerine and the lipid acid donor is very poor.And glycerine is easy to be adsorbed on lipase endoporus and enzyme molecular surface, to the avtive spot formation " shielding " of enzyme, has seriously reduced the catalytic activity of enzyme.
Summary of the invention
The object of the present invention is to provide a kind of enzyme process preparation 1,3-triglyceride technology has solved glycerine and has been easy to be adsorbed on lipase endoporus and enzyme molecular surface, to the avtive spot formation " shielding " of enzyme, seriously reduce the problem of the catalytic activity of enzyme, improved Enzymatic transformation efficient.
The present invention proposes with the trimethyl carbinol as reaction medium, utilize the esterification of lipase-catalyzed glycerine and lipid acid donor to prepare triglyceride and 1, the technology of 3-triglyceride, the lipid acid donor comprises lipid acid, the raw material of fatty acid short-chain ester and fatty acids or fatty acid short-chain ester.Its processing step is: with mol ratio is 1: 0.5～1: 3 glycerine and lipid acid donor, based on the trimethyl carbinol of lipid acid donor quality 20～200%, based on the lipase of lipid acid donor quality 2～20%, based on free fatty acids quality 10-100%'s
Molecular sieve mixes in any biochemical reactor that is suitable for enzyme reaction of packing into together, and temperature is controlled at 30～65 ℃, reacted 1～10 hour, glycerine can reach 70～90% to the transformation efficiency of triglyceride, and in these triglycerides 1, the content of 3-triglyceride can reach more than 60%.Described lipid acid donor comprises lipid acid, fatty acid ester or their mixture, and lipase can use separately, also can be used in combination by different lipase.
Lipase can be certain single fat enzyme, also can be the combination of different performance lipase; Described lipase comprises the lipase that derives from Candida antarctica, Thermomyces lanuginosus, Rhizomucor miehei or Rhizopusoryza.
Described lipid acid donor is lipid acid, fatty acid short-chain ester or both mixtures.
Described lipid acid is one or more the mixture that has in the lipid acid of 10～22 carbon atoms.
Described fatty acid short-chain ester is one or more the mixture in the methyl esters, ethyl ester, propyl ester, butyl ester, pentyl ester of above-mentioned lipid acid.
The invention has the beneficial effects as follows and adopt the trimethyl carbinol as reaction medium, glycerine can effectively be dissolved in the trimethyl carbinol system, and except that lipase, reaction is a homogeneous system, and Enzymatic transformation efficient significantly improves.
Embodiment
Further specify the present invention below by embodiment.
Embodiment 1
With mol ratio is 1: 1 glycerine and palmitinic acid, based on palmitinic acid quality 100%
Molecular sieve and based on the trimethyl carbinol of palmitinic acid quality 100%, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 50 ℃ after, adding is based on the immobilized lipase Novozym435 (deriving from Candida antarctica) of palmitinic acid quality 5%, reacted 3 hours, glycerine reaches 90% to the transformation efficiency of triglyceride, and wherein 1, the 3-triglyceride accounts for 45%.
Embodiment 2
With mol ratio 1: 0.5 glycerine and fatty acid methyl ester, and based on the trimethyl carbinol of fatty acid methyl ester quality 150%, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 50 ℃ after, adding was reacted 4 hours based on the immobilized lipase Lipozyme TL IM (deriving from Thermomyceslanuginosus) of fatty acid methyl ester quality 6%, and glycerine reaches 90% to the transformation efficiency of triglyceride, wherein 1, the 3-triglyceride accounts for 50%.
Embodiment 3
With mol ratio is 1: 2 glycerine and lipid acid (mixture of oleic acid and palmitinic acid), based on free fatty acids quality 50%
Molecular sieve, and based on the trimethyl carbinol of oleic acid quality 20%, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 50 ℃ after, adding was reacted 8 hours based on the immobilized lipase Lipozyme RM IM (deriving from Rhizomucor miehei) of oleic acid quality 10%, and glycerine reaches 70% to the transformation efficiency of triglyceride, wherein 1, the 3-triglyceride accounts for 50%.
Embodiment 4
With mol ratio is 1: 3 glycerine and acidifying oil (fatty acids 70%), based on free fatty acids quality 50%
Molecular sieve and based on the trimethyl carbinol of fatty-acid ethyl ester quality 50%, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 30 ℃ after, adding is based on the immobilized lipase Lipozyme TL IM of fatty-acid ethyl ester quality 10%, reacted 5 hours, glycerine reaches 80% to the transformation efficiency of triglyceride, and wherein 1, the 3-triglyceride accounts for 50%.
Embodiment 5
With mol ratio is 1: 3 glycerine and stearic acid, based on free fatty acids quality 50%
Molecular sieve, and based on the trimethyl carbinol of stearic acid quality 80%, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 65 ℃ after, adding was reacted 3 hours based on the immobilized lipase Novozym 435 of stearic acid quality 2%, and glycerine reaches 95% to the transformation efficiency of triglyceride, wherein 1, the 3-triglyceride accounts for 50%.
Embodiment 6
With mol ratio 1: 1 glycerine and lipid acid propyl ester, and based on the trimethyl carbinol of lipid acid propyl ester quality 200%, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 40 ℃ after, adding was reacted 1 hour based on the immobilized lipase Lipozyme RM IM of lipid acid propyl ester quality 10%, and glycerine reaches 90% to the transformation efficiency of triglyceride, wherein 1, the 3-triglyceride accounts for 50%.
Embodiment 7
With mol ratio is 1: 1 glycerine and oleic acid, based on free fatty acids quality 10%
Molecular sieve, and based on the trimethyl carbinol of oleic acid quality 100%, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 50 ℃ after, adding was reacted 3 hours based on the immobilized lipase Novozym 435 of oleic acid quality 2% and 5% immobilized lipase Lipozyme TL IM, and glycerine reaches 90% to the transformation efficiency of triglyceride, wherein 1, the 3-triglyceride accounts for 50%.
Embodiment 8
With mol ratio 1: 2 glycerine and fatty acid ester (mixture of fatty acid methyl ester and ethyl ester), and based on the trimethyl carbinol of fatty acid methyl ester quality 150%, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 55 ℃ after, adding is based on the immobilized lipase Novozym 435 of fatty acid methyl ester quality 1% and 4% immobilized lipase Lipozyme RM IM, reacted 3 hours, glycerine reaches 95% to the transformation efficiency of triglyceride, wherein 1, the 3-triglyceride accounts for 50%.
Embodiment 9
With mol ratio is 1: 3 glycerine and stearic acid, based on free fatty acids quality 30%
Molecular sieve, and based on the trimethyl carbinol of stearic acid quality 200%, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 60 ℃ after, adding was reacted 2 hours based on the immobilized lipase Lipozyme TL IM of stearic acid quality 2% and 3% immobilized lipase Lipozyme RM IM, and glycerine reaches 80% to the transformation efficiency of triglyceride, wherein 1, the 3-triglyceride accounts for 50%.
Claims (6)
1, a kind of enzyme process preparation 1, the technology of 3-triglyceride, it is characterized in that, processing step is: the glycerine and the lipid acid donor that with mol ratio are 1: 0.5～1: 3, the trimethyl carbinol based on lipid acid donor quality 20～200%, based on the lipase of lipid acid donor quality 2～20%, based on free fatty acids quality 10-100%'s
Molecular sieve mixes in any biochemical reactor that is suitable for enzyme reaction of packing into together, and temperature is controlled at 30～65 ℃, reacted 1～10 hour, glycerine can reach 70～90% to the transformation efficiency of triglyceride, and in these triglycerides 1, the content of 3-triglyceride can reach more than 60%; Described lipid acid donor comprises lipid acid, fatty acid ester or their mixture.
2, according to the described technology of claim 1, it is characterized in that, described lipase is biological lipase, and biological lipase comprises the lipase that derives from Candida antarctica, Thermomyceslanuginosus, Rhizomucor miehei or Rhizopus oryza.
According to the described technology of claim 1, it is characterized in that 3, described lipase uses separately, perhaps be used in combination with different lipase.
According to the described technology of claim 1, it is characterized in that 4, described lipid acid donor is the raw material of lipid acid, fatty acid short-chain ester or fatty acids or fatty acid short-chain ester.
According to the described technology of claim 4, it is characterized in that 5, described lipid acid is one or more the mixture that has in the lipid acid of 10～22 carbon atoms.
According to the described technology of claim 4, it is characterized in that 6, described fatty acid short-chain ester is for being one or more the mixture in the methyl esters, ethyl ester, propyl ester, butyl ester, pentyl ester.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008101050801A CN101260416A (en) | 2008-04-25 | 2008-04-25 | Technique for preparing 1,3-diglyceride by enzyme method |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008101050801A CN101260416A (en) | 2008-04-25 | 2008-04-25 | Technique for preparing 1,3-diglyceride by enzyme method |
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| Publication Number | Publication Date |
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| CN101260416A true CN101260416A (en) | 2008-09-10 |
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| CNA2008101050801A Pending CN101260416A (en) | 2008-04-25 | 2008-04-25 | Technique for preparing 1,3-diglyceride by enzyme method |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103074388A (en) * | 2012-12-21 | 2013-05-01 | 江南大学 | Method for catalytic synthesis of monoglyceride and diacylglycerol by lipase under ultrahigh pressure |
| CN103290076A (en) * | 2013-06-22 | 2013-09-11 | 青岛农业大学 | Method for preparing diglyceride through goose fat enzymolysis |
| CN103355419A (en) * | 2013-08-08 | 2013-10-23 | 陈昊然 | 1,3-diglyceride-enriched cream and preparation method thereof |
| CN104630296A (en) * | 2015-03-09 | 2015-05-20 | 杭州铎海科技有限公司 | Method for preparing 1,3-diglyceride through enzymolysis |
| CN107267563A (en) * | 2017-08-01 | 2017-10-20 | 东莞市感恩食品科技有限公司 | A kind of preparation method that the sweet ester of high content two is produced with biocatalysis technology |
| CN111394403A (en) * | 2020-03-18 | 2020-07-10 | 江苏瑞佳新材料有限公司 | Preparation method and application of fatty acid glycerol mixed ester |
| CN112513235A (en) * | 2018-06-05 | 2021-03-16 | 帝斯曼知识产权资产管理有限公司 | Process for producing diglycerides |
| CN112877376A (en) * | 2019-12-12 | 2021-06-01 | 上海安谱实验科技股份有限公司 | Synthetic method of 3-chloro-1, 2-propanediol fatty acid diester |
| CN116042736A (en) * | 2023-02-24 | 2023-05-02 | 江南大学 | Enzymatic production process of diglyceride |
-
2008
- 2008-04-25 CN CNA2008101050801A patent/CN101260416A/en active Pending
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103074388A (en) * | 2012-12-21 | 2013-05-01 | 江南大学 | Method for catalytic synthesis of monoglyceride and diacylglycerol by lipase under ultrahigh pressure |
| CN103290076A (en) * | 2013-06-22 | 2013-09-11 | 青岛农业大学 | Method for preparing diglyceride through goose fat enzymolysis |
| CN103290076B (en) * | 2013-06-22 | 2014-03-05 | 青岛农业大学 | Method for preparing diglyceride through goose fat enzymolysis |
| CN103355419A (en) * | 2013-08-08 | 2013-10-23 | 陈昊然 | 1,3-diglyceride-enriched cream and preparation method thereof |
| CN103355419B (en) * | 2013-08-08 | 2015-01-21 | 陈昊然 | 1,3-diglyceride-enriched cream and preparation method thereof |
| CN104630296A (en) * | 2015-03-09 | 2015-05-20 | 杭州铎海科技有限公司 | Method for preparing 1,3-diglyceride through enzymolysis |
| CN107267563A (en) * | 2017-08-01 | 2017-10-20 | 东莞市感恩食品科技有限公司 | A kind of preparation method that the sweet ester of high content two is produced with biocatalysis technology |
| CN112513235A (en) * | 2018-06-05 | 2021-03-16 | 帝斯曼知识产权资产管理有限公司 | Process for producing diglycerides |
| CN112513235B (en) * | 2018-06-05 | 2023-12-01 | 帝斯曼知识产权资产管理有限公司 | Process for producing diglyceride |
| CN112877376A (en) * | 2019-12-12 | 2021-06-01 | 上海安谱实验科技股份有限公司 | Synthetic method of 3-chloro-1, 2-propanediol fatty acid diester |
| CN112877376B (en) * | 2019-12-12 | 2022-08-30 | 上海安谱实验科技股份有限公司 | Synthetic method of 3-chloro-1, 2-propanediol fatty acid diester |
| CN111394403A (en) * | 2020-03-18 | 2020-07-10 | 江苏瑞佳新材料有限公司 | Preparation method and application of fatty acid glycerol mixed ester |
| CN116042736A (en) * | 2023-02-24 | 2023-05-02 | 江南大学 | Enzymatic production process of diglyceride |
| CN116042736B (en) * | 2023-02-24 | 2024-06-07 | 江南大学 | Enzymatic production method of diglyceride |
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